Network administrators often block user devices connected to an enterprise network from accessing unknown or malicious websites to enhance security, to increase productivity or to conserve network resources. For example, when a user device attached to an enterprise network sends a request to establish a Hypertext Transfer Protocol over Transport Layer Security (HTTPS) connection with an external website associated with a given Uniform Resource Locator (URL), an enterprise security device may intercept the request and abruptly terminate the HTTPS connection with the user device without notifying the user why the request was denied, or the browser may encounter HTTPS certificate errors if the browser is redirected via DNS to a web page hosted elsewhere that displays a block page. An end user therefore may not know why the connection was reset and, consequently, may repeatedly try to unsuccessfully reach the external website. Frustrated, the end user may use insecure interfaces to reach the external web site, compromising the security and integrity of the enterprise network. Furthermore, certificate errors train users to click through certificate errors, which is poor security practice. To eliminate the need for an end user to click through certificate errors, an end user or an IT administrator may install a root certificate on a host device. Doing so, however, is also poor security practice as it creates a security vulnerability that may be exploited by a man-in-the-middle attack.
Additionally, end users are increasingly using “bring your own devices” (BYOD) devices to connect to distinct enterprise domains, but may not be aware of the different access rules and policies enforced across those domains, potentially creating further security vulnerabilities that may cause significant damage to the networks themselves.